2-(3,4-Dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one as an Antibacterial, Antifungal and Antimycobacterial Agent

Article abstract of DOI:10.1002/jhet.2889

2-(3,4-Dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) thiazolidin-4-one has been selected as a target bio-active molecules. Newly synthesized compounds were screened with Eschericha coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442) for antibacterial, Candida albicans (MTCC 227), Aspergillus niger (MTCC 282), Aspergillus clavatus (MTCC 1323) for antifungal activity and H₃₇Rv for antimycobacterial activity. Compounds 3a, 3c, 3d, 3e, and 3h are potentially active against Staphylococcus aureus, while 3h is active against C.?albicans. Compounds 3d and 3f are active against H₃₇Rv for mycobacterium tuberculosis. Other possesses moderate to good activity. The structures of synthesized compounds were firmly established by well-defined elemental analyses (C, H, N, S/O) and spectral analysis technique likes, IR, ¹H NMR and GC–MS.

Full text of DOI:10.1002/jhet.2889

Month 2017
2-(3,4-Dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-
pyrazol-4-yl)methylene)thiazolidin-4-one as an Antibacterial, Antifungal
and Antimycobacterial Agent
b
Harshad Brahmbhatt,a,b Anjani K. Bhatt, Arun K. Das, Parimal Paul, and Sangita Sharma
a
a
a
*
aAnalytical Division and Centralized Instrument Facility, CSIR-Central Salt and Marine Chemicals Research Institute,
Bhavnagar 364 002, Gujarat, India
bHemchandracharya North Gujarat University, Patan 384 265, Gujarat, India
*
E-mail: sangitamem2000@gmail.com
Additional Supporting Information may be found in the online version of this article.
Received November 5, 2016
DOI 10.1002/jhet.2889
Published online 00 Month 2017 in Wiley Online Library (wileyonlinelibrary.com).
2-(3,4-Dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) thiazolidin-
4-one has been selected as a target bio-active molecules. Newly synthesized compounds were screened with
Eschericha coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96),
Streptococcus pyogenes (MTCC 442) for antibacterial, Candida albicans (MTCC 227), Aspergillus niger
(MTCC 282), Aspergillus clavatus (MTCC 1323) for antifungal activity and H37Rv for antimycobacterial
activity. Compounds 3a, 3c, 3d, 3e, and 3h are potentially active against Staphylococcus aureus, while 3h is
active against C. albicans. Compounds 3d and 3f are active against H37Rv for mycobacterium tuberculosis.
Other possesses moderate to good activity. The structures of synthesized compounds were firmly established
1
by well-defined elemental analyses (C, H, N, S/O) and spectral analysis technique likes, IR, H NMR and
GC–MS.
J. Heterocyclic Chem., 00, 00 (2017).
INTRODUCTION
inflammatory [24–26], anti-malarial, [27,28] and antiviral
activity [29,30].
During two decades of research and development
efforts, heterocyclic compound covers about one half of
over six million compounds recorded so far in chemical
abstracts. It is also known that heterocycles are part of
many important biochemical likes: DNA, RNA and
amino acids and vitamins. They have great attention of
researcher owing to their broad spectrum of biological
activities. As a result of these, heterocyclic chemistry is
one of the most interesting, complex and fascinating
branch of organic chemistry having largest and most
varied family of organic compounds. 4-Thiazolidinone
derivatives are well established and known to possess a
verity of pharmacological property such as anti-infective
agent [1,2], anti convulsant [3], sedative [4],
antimycobacterial [5–8], anti-inflammatory [9–12],
anti-HIV [13–15], anti-tumor [16], and anti-diabetic
activity [17,18].
4-Thiazolidinones and pyrazoles are highly active
bioactive compound in order to possess various class of
activity. In view to synthesis of highly potent bioactive
compounds, we intended to synthesize and to screen the
new
entities:
2-(3,4-dichlorophenylimino)-5-((3-(p-
substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene)
thiazolidin-4-one (3a–h), using 2-(3,4-dichlorophenylimino)
thiazolidin-4-one (1) and 1-phenyl-3-(p-substitutedphenyl)-
1H–pyrazole-4-carbaldehyde (2a–h).
MATERIAL AND METHOD
General.
The melting points of the synthesized
products were measured in open capillary on Mettler
Toledo FP 62 melting point apparatus (Metter
Toledo-Switzerland) and were uncorrected. Homogeneity
of the compound was checked by thin-layer
chromatography. Solvent system of Hexane: Ethyl acetate
(8:2) was used for thin-layer chromatography, and the
Various derivatives of pyrazoles are synthesized and
screened for various pharmacological activities like
antimicrobial [19–22], anticonvulsant [23], anti-
© 2017 Wiley Periodicals, Inc.

H. Brahmbhatt, A. K. Bhatt, A. K. Das, P. Paul, and S. Sharma
Vol 000
spots were visualized under UV light. The Fourier
Antimycobacterial activity.
Antimycobacterial activity
transform infrared (FT-IR) spectra’s were recorded on a
Perkin Elmer – Spectrum GX FT-IR System (PE – USA),
screening of novel synthesized compound was carried out
in vitro against a highly virulent H37Rv strain of
Mycobacterium tuberculosis. It was performed according
to the Lowenstein–Jensen medium (conventional
method). The time duration for media incubation was
4 weeks. Triplicate screenings were performed for all at
250-μg/mL concentration of compound. “Isoniazid” was
used as a standard drug for antimycobacterial activity.
The data are as shown in (Fig. 3).
1
using KBr pellets in the range of 4000–400 cmÀ1. H
spectra were recorded on 200-MHz Bruker Avance DPX
NMR systems. Chemicals shifts were expressed in δ
(ppm) relative to Tetramethylsilane as an internal standard
using DMSO-d6 as solvent. Elemental analyses of the
newly synthesized compounds were performed on Perkin
Elmer-2400 C, H, N, S/O analyzer (PE-USA). Elemental
analyses of all compounds were in well conformity with
the calculated values. The mass spectra were scanned on
a Shimadzu QP2010 spectrometer (Shimadzu-Japan) that
was equipped with a direct inlet probe. Mass detector
was operated at 70 eV. All the required chemicals of high
purity were purchased from Qualigens.
General method. Synthesis of 2-(3,4-dichlorophenylimino)
thiazolidin-4-one (1).
The synthesis of 2-(3,4-
dichlorophenylimino)thiazolidin-4-one compound was
prepared according to [32].
Synthesis of 1-phenyl-3-(p-substitutedphenyl)-1H–pyrazole-
4-carbaldehydes (2a–h). The synthesis of 1-phenyl-3-(p-
substitutedphenyl)-1H–pyrazole-4-carbaldehydes
com-
Biological assay. Antibacterial activity.
The newly
pounds was synthesized according to [33].
synthesized compounds were examined for their
antibacterial potency against Gram positive bacteria
Staphylococcus aureus (MTCC-96), Streptococcus
pyogenes (MTCC-442) and Gram negative bacteria
Escherichia coli (MTCC-443), Pseudomonas aeruginosa
(MTCC-1688). They were procured from Institute of
Microbial Technology, Chandigarh. Serial broth dilution
method was used for the antibacterial screening [31].
Triplicate antibacterial screening data were generated for
molecules (3a–h) against the aforementioned bacterial
strains at different concentration levels of 1000, 500,
200,100, 50, 25, 12.5 ppm as shown in (Fig. 2). The
entities that were found to be active in initial screening
were diluted in the same way to obtain 100, 50, 25,
12.5 ppm concentrations. Bacterial cultures growth was
monitored after 24 and 48 h. The lowest concentration at
which no further growth is observed after spot subculture
was considered as minimum inhibitory concentration
(MIC) of specific molecule. Highest dilution, which
shows at least 99% inhibition was considered as MIC. It
is also known as minimum bactericidal concentration.
The test mixture should contain at least 108 cells/mL.
“Ampicillin” was used as a standard drug for evaluating
antibacterial activity that have (100, 100, 250, and
100 ppm) MIC values against E. coli, P. aeruginosa,
Synthesis of 2-(3,4-dichlorophenylimino)-5-((3-(p-substi-
tutedphenyl)-1-phenyl-1H-pyrazol-4-yl) methylene) thiazolidin-
4-one (3a–h).
In round bottom flask, a solution of
2-(3,4-dichlorophenylimino)thiazolidin-4-one (1) (10 mM)
and anhydrous sodium acetate (10 mM), 1-phenyl-3-(p-
substituted phenyl)-1H–pyrazole-4-carbalde-hyde (2a–h)
(10 mM) in ethanol were heated under reflux for 6 h.
Reaction was monitored using thin-layer chromatography to
confirm the completion of reaction. Crude product was
washed with plenty of water, isolated by filtration and re-
crystallized from ethanol to obtain yellow crystalline solid
product (3a–h).
Physical and spectral data. 2-(3,4-Dichlorophenylimino)-
5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one
(3a). Yield 85%; Yellow crystalline solid; mp > 300°C; IR
(KBr, cmÀ1) ν: 3414 (NH- Stretching), 3039 (Ar-H
stretching, pyrazole –H stretching), 1723 (C═O stretching),
1601, 1533, 1468 (C═N, C═C, aromatic ring), 1304 (C═S
1
stretching), 690 (C-S-C linkage); H NMR (DMSO-d6) δ
(ppm): 8.65 (s,1H, ─C═CH group in pyrazole ring),
7.06–8.18 (m, 15H, Ar─H, C─NH, ÀC═CH); MS: m/z:
491 (M+), 319, 290, 186, 145; Anal. Calcd for
C25H16Cl2N4OS (491.4) (%): C, 61.11; H, 3.28; N, 11.40;
S, 6.53. Found: C, 61.29; H, 3.02; N, 11.52; S, 6.68.
2-(3,4-Dichlorophenylimino)-5-((1-phenyl-3-p-tolyl-1H-
pyrazol-4-yl)methylene)thiazolidin-4-one (3b).
Yield 76%;
S. aureus, and S. pyogenes, respectively.
Antifungal activity. Compounds (3a–h) were screened in
yellow crystalline solid; mp > 300°C; IR (KBr, cmÀ1) ν:
3411 (NH- Stretching), 3045 (Ar─H stretching, pyrazole
─H stretching), 1721 (C═O stretching), 1600, 1533, 1468
(C═N, C═C, aromatic ring), 1302 (C═S stretching), 684
(C-S-C linkage); 1H NMR (DMSO-d6) δ (ppm): 8.63
(s, 1H, ─C═CH group in pyrazole ring), 7.07–8.10
(m, 14H, Ar─H, C─NH, ÀC═CH), 2.40 (s,Ar─CH3
pyrazole ring); MS: m/z: 505 (M+), 319, 290, 276, 186;
Anal. Calcd for C26H18Cl2N4OS (505.4) (%): C, 61.79;
H, 3.59; N, 11.09; S, 6.34;. Found: C, 61.66; H, 3.55;
N, 11.21; S, 6.42.
triplicate for their antifungal potency against Candida
albicans, Aspergillus niger and Aspergillus clavatus at
various concentrations of 1000, 500, 200, and 100 ppm as
shown in (Fig. 2). Specific concentrations at which have at
least 99% inhibition were considered as MIC. It is also
known as minimum fungicidal concentration (MFC). The
test mixture should contain 108 spores/mL. “Griseofulvin”
having (500, 100 and 100 ppm) MIC for C. albicans,
A. niger and A. clavatus for respective fungal strains was
considered as a reference drug for antifungal screening.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
2-(3,4-Dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-pyrazol-
4-yl)methylene)thiazolidin-4-one as Bioactive Molecules
2-(3,4-Dichlorophenylimino)-5-((3-(4-hydroxyphenyl)-
1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one
(3c). Yield 78%; yellow crystalline solid; mp > 300°C;
(C═N, C═C, aromatic ring), 1301 (C═S stretching), 684
(C-S-C linkage); 1H NMR (DMSO-d6) δ (ppm): 8.60 (s, 1H,
─C═CH group in pyrazole ring), 7.03–7.95 (m, 14H,
Ar─H, C─NH, ─C═CH); MS: m/z: 526 (M+), 356, 310,
275, 231, 172; Anal. Calcd for C25H15Cl3N4OS (525.8)
(%): C, 57.10; H, 2.88; N, 10.65; S, 6.10. Found: C, 57.22;
IR (KBr, cmÀ1) ν: 3500 (NH- Stretching), 3046 (Ar─H
stretching, pyrazole ─H stretching), 1713 (C═O
stretching), 1600, 1527, 1469 (C═N, C═C, aromatic
ring), 1312 (C═S stretching), 684 (C-S-C linkage); 1H
NMR (DMSO-d6) δ (ppm): 8.61 (s, 1H, ─C═CH group
in pyrazole ring), 7.04–7.96 (m, 14H, Ar-H, C-NH,
ÀC═CH); MS: m/z: 507 (M+), 319, 290, 257, 186;
Anal. Calcd for C25H16Cl2N4O2S (507.4) (%): C, 59.18;
H, 3.18; N, 11.04; S, 6.32. Found: C, 59.39; H, 3.11;
N, 11.08; S, 6.29.
H, 2.72; N, 10.76; S, 6.17.
2-(3,4-Dichlorophenylimino)-5-((3-(4-methoxyphenyl)-1-phenyl-
1H-pyrazol-4-yl)methylene)thiazolidin-4-one (3h).
Yield 67%;
yellow crystalline solid; mp > 300°C; IR (KBr, cmÀ1) ν:
3410 (NH- Stretching), 3042 (Ar─H stretching, pyrazole ─H
stretching), 1718 (C═O stretching), 1605, 1529, 1464 (C═N,
C═C, aromatic ring), 1302 (C═S stretching), 683 (C-S-C
linkage); 1H NMR (DMSO-d6) δ (ppm): 8.65 (s, 1H,
─C═CH group in pyrazole ring), 7.06–7.96 (m, 14H, Ar─H,
C─NH, ÀC═CH), 3.84(s, 3H, Ar-OCH3 pyrazole ring); MS:
m/z: 521(M+), 356, 306, 275, 231, 172; Anal. Calcd for
C25H15Cl3N4OS (521.4) (%): C, 59.89; H, 3.48; N, 10.75; S,
6.15. Found: C, 59.60; H, 3.31; N, 10.58; S, 6.03.
2-(3,4-Dichlorophenylimino)-5-((3-(4-nitrophenyl)-1-phenyl-
1H-pyrazol-4-yl)methylene)thiazolidin-4-one (3d).
Yield
82%; yellow crystalline solid; mp 289–291°C; IR (KBr,
cmÀ1) ν: 3445 (NH- Stretching), 3044 (Ar─H stretching,
pyrazole –H stretching), 1722 (C═O stretching), 1608,
1533, 1469 (C═N, C═C, aromatic ring), 1304 (C═S
1
stretching), 681 (C-S-C linkage); H NMR (DMSO-d6) δ
(ppm): 8.66 (s, 1H, ─C═CH group in pyrazole ring), 7.04–
8.40 (m, 14H, Ar-H, C-NH, ─C═CH); MS: m/z: 536 (M+),
506, 321, 292, 186; Anal. Calcd for C25H15Cl2N5O3S
(536.4) (%): C, 55.98; H, 2.82; N, 13.06; S, 5.98. Found:
C, 56.12; H, 2.98; N, 13.13; S, 5.87.
2-(3,4-Dichlorophenylimino)-5-((3-(4-fluorophenyl)-1-
phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one
(3e). Yield 66%; yellow crystalline solid; mp > 300°C;
RESULT AND DISCUSSION
Chemistry.
This study describe the synthesis,
characterization and antimicrobial screening of novel
2-(3,4-dichlorophenylimino)-5-((3-(p-substitutedphenyl)-
1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one
derivatives. 3,4-Dichloroaniline and ammonium
thiocyanate reacted to produce 1-(3,4-dichlorophenyl)
thiourea, which further reacted with monochloroacetic
acid to make 2-(3,4-dichlorophenylimino) thiazolidin-
4-one (1) [32]. According to Vilsmeier–Haack reaction, 1-
phenyl-3-(p-substituted phenyl)-1H–pyrazole-4-carbaldehyde
derivatives (2a–h) were synthesized from 4-substituted
acetophenone, phenyl hydrazine, phosphorous oxychloride
and dimethylformamide. Substituted acetophenone was
reacted with phenyl hydrazine to produce hydrazones,
which reacted with formylating solution (dimethyl
formamide and phosphorous-oxychloride solution) to
fabricate 1-phenyl-3-(p-substituted phenyl)-1H–pyrazole-4-
IR (KBr, cmÀ1) ν: 3402 (NH- Stretching), 3119 (Ar-H
stretching, pyrazole –H stretching), 1702 (C═O
stretching), 1600, 1531, 1446 (C═N, C═C, aromatic
ring), 1338 (C═S stretching), 679 (C-S-C linkage); 1H
NMR (DMSO-d6) δ (ppm): 8.62 (s, 1H, ─C═CH group
in pyrazole ring), 7.05–7.96 (m, 14H, Ar-H, C-NH,
ÀC═CH); MS: m/z: 509 (M+), 492, 323, 294, 233, 191;
Anal. Calcd for C25H15Cl2FN4OS (509.4) (%): C, 58.95;
H, 2.97; N, 11.00; S, 6.29. Found: C, 58.73; H, 3.17;
N, 11.36; S, 6.39.
5-((3-(4-Bromophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-
2-(3,4-dichlorophenylimino)thiazolidin-4-one (3f).
Yield
79%; Yellow crystalline solid; mp 288–290°C; IR (KBr,
cmÀ1) ν: 3414 (NH- Stretching), 3050 (Ar─H stretching,
pyrazole ─H stretching), 1723 (C═O stretching), 1605,
1532, 1442 (C═N, C═C, aromatic ring), 1305 (C═S
carbaldehyde
thiazolidin-4-one (1) and 1-phenyl-3-(p-substituted
phenyl)-1H–pyrazole-4-carbaldehyde (2a–h) were
[33].
2-(3,4-Dichlorophenylimino)
1
subjected to Knoevenagel condensation to form 2-(3,4-
dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-
phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one
(3a–h) (Fig. 1). New molecules (3a–h) were
confirmed using FT-IR, FT-NMR and mass spectrometry.
The IR band observed around 1300–1350 cmÀ1 is
attributed to C═S stretching vibration of thiazole ring.
Bands at about around 1570–1610 cmÀ1 is attributed to
C═N stretching vibration of pyrazole moiety. Strong
band in the region 1695–1730 cmÀ1 supports the
presence of ─C═O stretching in thiazolidinone ring.
stretching), 684 (C-S-C linkage); H NMR (DMSO-d6) δ
(ppm): 8.64 (s, 1H, ─C═CH group in pyrazole ring),
7.05–7.96 (m, 14H, Ar─H, C─NH, ─C═CH); MS: m/z:
554 (M+– OÀ), 386, 356, 275, 231, 170; Anal. Calcd for
C25H15Cl2BrN4OS (570.3) (%): C, 52.65; H, 2.65; N,
9.82; S, 5.62. Found: C, 52.81; H, 2.42; N, 9.72; S, 5.78.
5-((3-(4-Chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-
2-(3,4-dichlorophenylimino)thiazolidin-4-one (3g).
Yield
81%; yellow crystalline solid; mp > 300°C; IR (KBr, cmÀ1
)
ν: 3413 (NH- Stretching), 3044 (Ar─H stretching, pyrazole
─H stretching), 1723 (C═O stretching), 1604, 1532, 1440
Journal of Heterocyclic Chemistry
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H. Brahmbhatt, A. K. Bhatt, A. K. Das, P. Paul, and S. Sharma
Vol 000
Figure 1. Synthetic pathway of 2-(3,4-dichlorophenylimino)-5-((3-(p-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene) thiazolidin-4-one: (3a–h).
[Color figure can be viewed at wileyonlinelibrary.com]
Proton-NMR and mass spectral data of compound (3a–h)
are shown in “Materials and Method” section. Chemical
shift δ at around 8.7–8.5 ppm indicate the presence of
─C═CH group in pyrazole ring. All the entities were
analyzed satisfactory for (C, H, N, S/O) elemental analysis.
Antibacterial activity.
The results of antibacterial
screening of newly synthesized compounds are presented in
Figure 2. For the antibacterial activity, we have taken four
different bacterial strains like, E. coli, P. aeruginosa,
S. aureus, and S. pyogenes. For, E. coli, compounds 3a
and 3e (R’ = 4-H and 4-F) possess good activity, while
compounds 3c, 3f, and 3g (R’ = 4-OH, 4-Br, and 4-Cl,
respectively) possess moderate activity as compared with
the standard drug ampicillin, For P. aeruginosa,
compound 3a (R’ = 4-H) possesses good activity, while
compounds 3c, 3d, 3e, 3f and 3g (R’ = 4-OH, 4-NO2, 4-F,
4-Br and 4-Cl, respectively) possess moderate activity as
compared to the standard drug ampicillin. For S. aureus,
compounds 3a, 3c, 3e and 3h (R’ = 4-H, 4-OH, 4-F, and
4-OCH3, respectively) possess good activity, while
compound 3d (R’ = 4-NO2) possesses very good activity
Antimicrobial activity evaluation.
Approach to the
synthesis of new bioactive entities required high scientific
attitude, proper projection towards the recent problems,
creation of huge knowledge based data bank, and technically
designed effort. Antimicrobial activity of synthesized
compound was performed against four different bacterial
strains like, E. coli, P. aeruginosa, S. aureus and S. pyogenes
and three different fungi like, C. albicans, A. niger and
A. clavatus. “Ampicillin” and “Griseofulvin” were used as
positive control for bacteria and fungi respectively, and
solvent control was also to know the activity of solvent.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
2-(3,4-Dichlorophenylimino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-pyrazol-
4-yl)methylene)thiazolidin-4-one as Bioactive Molecules
Figure 2. Antibacterial and Antifungal activity of compound 2-(3,4-dichlorophenylimino)-5-((3-(p-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl)
methylene) thiazolidin-4-one: (3a–h). [Color figure can be viewed at wileyonlinelibrary.com]
as compared with the standard drug ampicillin. For
S. pyogenes, compounds 3d, 3e, and 3h (R’ = 4-NO2, 4-F
and 4-OCH3, respectively) possess moderate activity as
compared with the standard drug ampicillin.
respectively) possess good activity as compared with the
standard drug Griseofulvin,
Antimycobacterial activity.
The antimycobacterial
screening of newly synthesized compounds are presented
in Figure 3. Highly virulent H37Rv strain of
Mycobacterium tuberculosis was selected for anti-
tuberculosis activity screening. Compounds 3d and 3f
(R’ = 4-NO2 and 4-Br, respectively) possess very good
antimycobacterial activity, while compounds 3c, 3e, and
3g (R’ = 4-OH, 4-F, and 4-Cl, respectively) possess good
antimycobacterial activity as compared with Isoniazid.
Antifungal activity.
Antifungal screening of data of
newly synthesized compounds is shown in Figure 2. For
the antifungal activity, we have taken three different
fungal strains like C. albicans, A. niger, and A. clavatus.
For, C. albicans, compounds 3a and 3e (R’ = 4-H and
4-F, respectively) possess very good activity, while
compounds 3b and 3h (R’ = 4-CH3 and 4-OCH3,
AnƟmycobacterial acƟvity chart
100
90
80
70
60
50
40
30
20
10
0
3a
3b
3c
3d
3e
3f
3g
3h
Isoniazid
Compound and standard
Figure 3. Antimycobacterial activity of compound 2-(3,4-dichlorophenylimino)-5-((3-(p-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene)
thiazolidin-4-one: (3a–h). [Color figure can be viewed at wileyonlinelibrary.com]
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

H. Brahmbhatt, A. K. Bhatt, A. K. Das, P. Paul, and S. Sharma
Vol 000
[8] Babaoglu, K.; Page, M. A.; Jones, V. C.; McNei, M. R.; Dong,
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Alsayed, S. S. Bioorg Chem 2016, 64, 1.
CONCLUSION
Newly synthesized compounds series of 2-(3,4-
dichlorophenylimino)-5-((3-(p-substituted
phenyl)-1-
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phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one were
synthesized from 2-(3,4-dichlorophenylimino)thiazolidin-4-
one (1) and 1-phenyl-3-(p-substituted phenyl)-1H–
pyrazole-4-carbaldehydes (2a–h). Analytical and spectral
data (FT-IR, 1H–NMR, GC–MS) of all the synthesized
compounds were in full agreement with the anticipated
structure. Assessment of the antimicrobial results of
synthesized compounds (3a–h) accomplished that the
pyrazole derivatives in 2-(3,4-dichlorophenylimino)
thiazolidin-4-one (1) enhanced their antimicrobial activity.
Most of the compounds were found to be active against
tested micro-organism. Especially compounds 3a, 3c, 3d,
3e, and 3h (R’ = 4-H, 4-OH, 4-NO2, 4-F and 4-OCH3,
respectively) have potent activity against S. aureus, while
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compound 3h (R’
= 4-OCH3) is excellent against
C. albicans. Overall, a series of 2-(3,4-dichloropheny
limino)-5-((3-(p-substitutedphenyl)-1-phenyl-1H-pyrazol-4-
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to moderate activity.
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Acknowledgments. Authors are thankful for the help and co-
operation of the Analytical Division and Centralized Instrument
Facility, CSIR-CSMCRI and “Microcare laboratory and TRC” –
Surat for carrying out microbial studies. Dr. Amit Dodiya is also
acknowledged for his valuable guidance.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet